Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86716473, compound

HRID 2275426Notes

Reaction equation

HRID 2275426 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH2:29]OC1CCCCO1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S([O-])(=O)=[O:45])=CC=1.C1C=C[NH+]=CC=1>>[Si:1]([O:18][CH:19]([OH:45])[CH2:20][CH2:21][CH2:22][C:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86716474HCID 86716474, compound

Product 1

HCID 86716473HCID 86716473, compoundYield 72%

Procedure

Following the procedure reported to prepare analog 25, 1-(tert-butyldiphenylsilyloxy)-11-(tetrahydro-2H-pyran-2-yloxy)undec-6-yne was cleaved with a catalytic amount of PPTS to give the title compound (72%) as a colorless liquid. TLC: EtOAc/hexanes (3:7), Rf˜0.43; 1H NMR (300 MHz) δ 7.64-7.68 (m, 4H), 7.34-7.42 (m, 6H), 3.62 (t, J=5.6 Hz, 4H), 2.06-2.22 (m, 4H), 1.64-1.50 (m, 10H), 1.04 (s, 9H); 13C NMR (100 MHz) δ 135.82, 134.33, 129.77, 127.84, 80.77, 80.11, 64.06, 62.69, 32.35, 32.10, 29.10, 27.12, 25.60, 25.33, 18.97, 18.78. HRMS calcd for C27H39O2Si [M+1]+ 423.2719. found 423.2718.

Sources & evidence

ORD record
ord-ff91f126fa3342e88a71dca0397f0090
Source dataset
uspto-grants-2015_09
Patent number
US09127027B2

Reaction notes

Loading…